Tributylphosphine → HCID 131729883, compound

HRID 884389Notes

Reaction equation

HRID 884389 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14]O)[N:9]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Se:32]C#N)([O-:25])=[O:24].C(P(CCCC)CCCC)CCC>C1COCC1.N1C=CC=CC=1.CC(OC)(C)C>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][Se:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N+:23]([O-:25])=[O:24])[N:9]1[C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 3

HCID 13831TributylphosphineHCID 1039312-Nitrophenyl selenocyanateHCID 123164143HCID 123164143, compound

Product 1

HCID 131729883HCID 131729883, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 4.18 g of alcohol 184 (13.3 mmol) in 50 ml of anhydrous THF and 17 ml of anhydrous pyridine was added with 3.31 g of ortho-nitrophenyl selenocyanate (14.6 mmol, 1.1 eq.). Slow dropwise addition of 4.30 ml of tri-n-butylphosphine (17.3 mmol, 1.3 eq.) with cooling in an ice bath resulted in a dark-red solution. After stirring for 30 min at RT, the batch was diluted with 200 ml of MTBE and filtered over a small amount of silica gel. Concentrating the filtrate afforded a brownish-yellow residue that was purified using silica gel column chromatography (EE/CH 1:4), thereby isolating 6.06 g of the selenyl ether 47 (12.1 mmol, 92%) as an intensely yellow colored oil.

Workup

  1. temperaturewith cooling in an ice bath
  2. customresulted in a dark-red solution
  3. filtrationfiltered over a small amount of silica gel
  4. concentrationConcentrating the filtrate
  5. customafforded a brownish-yellow residue that
  6. customwas purified

Sources & evidence

ORD record
ord-d22b0a23b4114606884c06ed155156ab
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

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